Hydrochloric Acid → 3-(1,1-Dimethylethyl)-L-phenylalanine 1,1-dimethylethyl ester

HRID 429904Notes

Reaction equation

HRID 429904 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])([CH3:5])([CH3:4])[CH3:3].[CH3:18][C:19](=[CH2:21])[CH3:20].OS(O)(=O)=O.Cl>O1CCOCC1>[C:2]([C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][C@@H:10]([C:12]([O:14][C:19]([CH3:21])([CH3:20])[CH3:18])=[O:13])[NH2:11])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 20706030HCID 20706030, compound

Product 1

HCID 207060443-(1,1-Dimethylethyl)-L-phenylalanine 1,1-dimethylethyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to example 54, 0.50 g of 3-tert-butyl-L-phenylalanine-HCl was treated with 30 mL of isobutylene in 25 mL of 1,4-dioxane in the presence of 0.4 mL of conc. H2SO4. Work-up in the usual manner followed by acidification of the free amine with ethereal HCl afforded 0.53 g (87%) of tert-butyl 3-tert-butyl-L-phenylalaninate.HCl as a light yellow foam.

Sources & evidence

ORD record
ord-abfbc0e13deb45ce9fc90337fc2e1f2b
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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